Grommets are often used to mount an elongate cable (designated at 20 in FIGS. 5A and 5B, typically a fiber optic, coaxial, twisted pair, power, or hybrid cable) within in the internal bore of a cable gland 22 mounted in a wall of an enclosure 24. In this environment, a grommet is used to customize the sealing of the gland 22 and the cable 20. However, it can be difficult to insert the end of a typical grommet 10′ into the gland 22 (as in FIG. 4), because (a) the outer diameter of the grommet 10′ is the approximate size of the gland opening and (b) the grommet 10′ is typically formed of a pliable rubber that generates considerable friction when in contact with the gland 22. As such, insertion of the grommet 10′ into the gland 22 often involves bending the grommet 10′ to get one edge in initially, which can be particularly difficult for thicker grommets. As such, it may be desirable to address the difficulty of grommet installation.